(Z)-1-(3-bromo-4-methoxyphenyl)-N-phenylmethanimine oxide | 1314208-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-1-(3-bromo-4-methoxyphenyl)-N-phenylmethanimine oxide
• CAS: 1314208-85-9
• 化学式: C₁₄H₁₂BrNO₂
• 分子量: 306.159
• InChiKey: MXAQCUYXVKEWSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-(3-bromo-4-methoxyphenyl)-N-phenylmethanimine oxide 、 parthenin 以 苯 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents

  摘要：

  Several novel Spiro derivatives of parthenin (1) have been synthesized by the dipolar cycloaddition using various dipoles viz; benzonitrile oxides, nitrones and azides with exocyclic double bond of C ring (alpha-methylene-gamma-butyrolactone). Majority of the compounds exhibited improved anti-cancer activity compared to the parthenin, when screened for their in vitro cytotoxicity against three human cancer cell lines viz., SW-620, DU-145 and PC-3. In vivo screening of select analog revealed improved anti-cancer activity with low mammalian toxicity as compared to parthenin. The results of the cytotoxicity pattern of these derivatives reveals the SAR of these sesquiterpinoid lactones and possible role of alpha,beta-unsaturated ketone of parthenin in inhibiting NF-kB. A mechanistic correlation of anti-cancer activity along with in vivo and western blotting experiments has been described. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.030

文献信息

• Synthesis and anticancer activity of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of α-santonin
  作者：Jabeena Khazir、Parvinder Pal Singh、D. Mahendhar Reddy、Irfan Hyder、Syed Shafi、S.D. Sawant、Gousia Chashoo、Ajay Mahajan、M.S. Alam、A.K. Saxena、S. Arvinda、B.D. Gupta、H.M. Sampath Kumar

  DOI：10.1016/j.ejmech.2013.01.003

  日期：2013.5

  In the present study, novel Spiro derivatives of alpha-santonin were prepared and tested for their anticancer activity against a panel of six human cancer cell lines. Spiro-isoxazoline and spiro-isoxazolidine derivatives have been generated on C-ring of alpha-santonin (alpha-methylene-gamma-butyrolactone) by the 1,3-dipolar cycloaddition of alpha-santonin derivative 6 with nitrile oxides 7 and nitrones 9 respectively. Among all, compound 10b '' had shown IC50 of 0.01, 0.5 and 0.3 mu M against PC-3, THP-1 and MCF-7 cell lines respectively. Further, flow cytometry studies showed that PC-3 cells treated with the spiro-isoxazolidine derivative 10b '' were arrested in the sub G1 phase of the cell cycle in a concentration dependent manner. The spiro-isoxazolidine derivative 10b '' also showed concentration dependent inhibitory activity against NF-kappa B, p65 with 57% inhibition in 24 h at 10 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.